Top Tech Jobs & Startup Jobs in Chicago, IL

Leads global revenue accounting, commissions, quoting, accounts receivable, billing, collections, and cash application. Owns ASC 606 and ASC 340 compliance across SaaS, professional services, and usage-based models. Partners with Sales, Legal, RevOps, Finance, and executives on contract structure, controls, reporting, audits, and strategic initiatives. Develops accounting and quote analyst teams while improving revenue predictability, cash flow, DSO, and quote-to-cash processes.

Leads end-to-end AI training projects, from customer scoping through execution. Responsibilities include sourcing specialized contributors, managing contributor communities, designing operational workflows, tracking performance and project economics, communicating with customers, mitigating risks, and building scalable processes for a growing AI Training business.

Drive revenue through strategic partnerships with ISVs, agencies, and consulting firms. Recruit and develop agency partners, sell directly to targeted agencies, manage pipeline and quota, create joint go-to-market plans, lead negotiations, and drive partner-sourced and co-sell revenue. Collaborate with Sales, Marketing, Product, Customer Success, and Enablement to activate partners and expand routes to market.

Define and execute the market strategy for UserTesting’s AI solutions. Own positioning, messaging, value propositions, go-to-market plans, sales enablement, customer and buyer research, competitive differentiation, thought leadership, and market feedback loops. Translate complex AI workflows and human-judgment applications into compelling solutions for technical enterprise buyers, while influencing product and company strategy through cross-functional leadership.

Deploy and maintain AI enablement infrastructure (MCP servers, AI agents, AI features in SaaS), manage service accounts and API keys, automate and containerize services, support enterprise IT systems, document integrations and runbooks, and mentor IT support staff.